Sodium Fluoride → HCID 22940130, compound

HRID 1821684Notes

Reaction equation

HRID 1821684 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:4]([O:16][CH3:17])[CH:3]=1.[CH2:18]([Sn](CCCC)(CCCC)CCCC)[CH:19]=[CH2:20].C(OCC)(=O)C.[F-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:20]([C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:4]([O:16][CH3:17])[CH:3]=1)[CH:19]=[CH2:18]

Participants

7

Reactant 4

HCID 5235Sodium FluorideHCID 8857Ethyl AcetateHCID 90628AllyltributylstannaneHCID 229401366-Chloro-4-methoxy-3-(2-methylphenoxy)pyridazine

Product 1

HCID 22940130HCID 22940130, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In toluene (4 mL) was dissolved 200 mg (0.797 mmol) of 6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in Example 2 (1), 305 mg (0.921 mmol) of allyl-(tributyl)tin, and then, 96.8 mg (0.0838 mmol) of tetrakis-(triphenylphosphine)palladium were successively added to the solution at room temperature, and the resulting mixture was refluxed for 3 hours and 20 minutes. The reaction mixture was allowed to stand at room temperature overnight, and then, ethyl acetate, water and sodium fluoride were added to the mixture and the resulting mixture was stirred for 2 hours. The mixture was filtered through Celite, ethyl acetate was added to the filtrate, then the organic layer was separated, and washed successively with water and brine. After drying over anhydrous sodium sulfate, the solvent was removed. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate, gradient) to obtain 62.1 mg (0.243 mmol, Yield: 30.5%) of 6-allyl-4-methoxy-3-(2-methylphenoxy)pyridazine.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours and 20 minutes
  2. filtrationThe mixture was filtered through Celite, ethyl acetate
  3. additionwas added to the filtrate
  4. customthe organic layer was separated
  5. washwashed successively with water and brine
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe solvent was removed
  8. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate, gradient)

Sources & evidence

ORD record
ord-f9b3892777e843f09b598f90f3f312b7
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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